The Trail Blazers once again acquired Jrue Holiday in a deal with the Celtics right before the 2025 NBA Draft. Holiday drew interest from multiple teams around the league, though the Celtics shipped him to Portland for Anfernee Simons and two second-round draft picks.
But this time, the Blazers plan to keep the veteran guard in Holiday on their roster, per NBA insider Jake Fischer. Portland impressed during the second half of the season as the young team gets a two-time NBA champion to help lead the way. While there were some questions of if Portland could flip Holiday again, that doesn’t appear to be the case.
This marks the second time the Blazers acquired Holiday in a trade. The first time came in the Damian Lillard blockbuster deal with the Bucks ahead of the 2023-24 season. But, back then, the Blazers were set to rebuild, so Holiday was bound to get traded elsewhere.
That’s when the Celtics sensed an opportunity, dealing for Holiday before the start of training camp. The move worked out perfectly for Boston as Holiday played an important role to bring the 2024 NBA championship to the Celtics. Holiday ends his two-year Boston tenure having played in 131 games, averaging 11.8 points, 4.9 rebounds and 4.4 assists per game.
The Celtics were set to shed payroll this summer as Holiday was deep in trade rumors over the past several weeks. Considering Boston was entering a transition period, it was no surprise to see Holiday, 35, getting moved in the deal. He still has three years and $104 million still left on his contract.
Now, the Celtics can continue to slim down their payroll going forward. Holiday will go and be a mentor figure for a Blazers squad looking to take steps toward competitiveness.